Sodium borohydride → HCID 59648505, compound

HRID 1363263Notes

Reaction equation

HRID 1363263 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([C:8]2[S:20][C:11]3[NH:12][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:14][C:10]=3[CH:9]=2)=O)=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:8]2[S:20][C:11]3[NH:12][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:14][C:10]=3[CH:9]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 6451240Aluminum(III) ChlorideHCID 59648618HCID 59648618, compound

Product 1

HCID 59648505HCID 59648505, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a N2 and at rt, to a 40-mL scintillation vial fitted with a magnetic stir bar was added ethyl 2-(4-chlorobenzoyl)-6H-thieno[2,3-b]pyrrole-5-carboxylate (0.203 g, 0.61 mmol) in solution in 5 mL in THF. AlCl3 (0.22 g, 1.67 mmol, 2.75 equiv) and NaBH4 (0.116 g, 3.0 mmol, 5 eq.) are added in the same time. The mixture was heated to reflux for 2 h. The reaction was cooled to rt and solvent was evaporated. The crude product was purified via ISCO Companion (0-30% EtOAc/heptane over 30 min) to give ethyl 2-(4-chlorobenzyl)-6H-thieno[2,3-b]pyrrole-5-carboxylate (0.050 g). 1H NMR (400 MHz, CDCl3) δ ppm 1.39 (t, J=7.13 Hz, 3H) 4.11 (s, 2H) 4.37 (q, J=7.13 Hz, 2H) 6.71 (s, 1H) 7.00 (d, J=1.76 Hz, 1H) 7.18-7.23 (m, 2H) 7.27-7.32 (m, 2H) 9.41 (s, 1H).

Workup

  1. customUnder a N2 and at rt, to a 40-mL scintillation vial fitted with a magnetic stir bar
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 2 h
  4. customsolvent was evaporated
  5. customThe crude product was purified via ISCO Companion (0-30% EtOAc/heptane over 30 min)

Sources & evidence

ORD record
ord-38c9b9264661472eb9314eed722ea88a
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

Loading…